Synthesis of novel pyrano[2,3-f]chromene-dione derivatives using phosphoric acid-functionalized silica-coated Fe3O4 nanoparticles as a new reusable solid acid nanocatalyst

Abstract

In this research, the synthesis of novel indeno[1,2-b]pyrano[2,3-f]chromene-2,12(13H)-dione derivatives in the presence of a newly introduced magnetically recoverable nanosolid acid catalyst is reported. At the first, phosphoric acid-functionalized silica-coated Fe₃O₄ nanoparticles (Fe₃O₄@SiO₂-(CH₂)₃OPO₃H₂) were prepared and well characterized using infrared spectroscopy (FT-IR), X-ray diffraction (XRD), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), and energy-dispersive X-ray spectroscopy (EDS) techniques. Then, the catalytic activity of the prepared Fe₃O₄@ SiO₂-(CH₂)₃OPO₃H₂ nanocatalyst was investigated for the synthesis of novel indeno[1,2-b]pyrano[2,3-f]chromene-2,12(13H)-dione derivatives via a one-pot and three-component condensation between 5,7-dihydroxy-4-methylcoumarin, indane-1, 3-dione, and various aromatic aldehydes under solvent-free condition. All the products are unknown, and their characterization was performed with the spectral data information obtained from their FT-IR, ¹H and ¹³CNMR, elemental analysis, and their melting points. The reusability study of the introduced nanosolid acid catalyst showed that the catalytic stability is almost completely remained up to five consecutive runs.

Keywords: 5,7-Dihydroxy-4-methylcoumarin; Chromene; Indan-1,3-dione; Magnetic nanoparticle; Multi-component reaction; Recoverable catalyst.